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Application Area

D-Pyroglutamic acid ethyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Cyclic Amino Acids

Catalog number

BAT-007252

CAS number

68766-96-1

Molecular Formula

C7H11NO3

Molecular Weight

157.17

IUPAC Name

ethyl (2R)-5-oxopyrrolidine-2-carboxylate

Synonyms

D-Pyr-OEt; (R)-5-Oxopyrrolidine-2-carboxylic acid ethyl ester; D Pyr OEt

Appearance

Pale yellow crystal

Purity

≥ 98% (NMR)

Density

1.161 g/cm3

Melting Point

53-57 °C

Boiling Point

176 °C 12 mmHg(lit.)

Storage

Store at 2-8 °C

InChI

InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m1/s1

InChI Key

QYJOOVQLTTVTJY-RXMQYKEDSA-N

Canonical SMILES

CCOC(=O)C1CCC(=O)N1

D-Pyroglutamic acid ethyl ester is a synthetic derivative of pyroglutamic acid, which is a cyclic amino acid naturally occurring in proteins and peptides. This compound is typically used in research and applications related to biochemistry, pharmaceuticals, and biotechnology. It consists of a pyroglutamic acid backbone with an ethyl ester group attached to the carboxylate, which improves its solubility and bioavailability. D-Pyroglutamic acid ethyl ester is often employed as an intermediate in the synthesis of various peptides and as a reagent in peptide chemistry.

One of the key applications of D-Pyroglutamic acid ethyl ester is in peptide synthesis. Its high solubility and ability to stabilize certain peptide linkages make it an excellent building block for peptide chain elongation. In this context, it is used to enhance the efficiency of chemical reactions that involve peptide bonds, especially for the creation of complex, bioactive peptides. This is crucial in the development of pharmaceuticals and biologics that require precise peptide sequences.

D-Pyroglutamic acid ethyl ester also plays a role in drug delivery systems. Its esterification provides a means to modify the physicochemical properties of the molecule, allowing for improved penetration of biological barriers such as the blood-brain barrier. This property is particularly valuable in the development of targeted therapies for neurological diseases. Researchers are investigating its potential to be used in conjunction with other active pharmaceutical ingredients to enhance therapeutic efficacy.

In addition to its pharmaceutical applications, D-Pyroglutamic acid ethyl ester is utilized in cosmetic formulations. It is known for its potential to enhance skin hydration and promote the stabilization of proteins in skin cells. This makes it a valuable ingredient in anti-aging products and formulations designed to improve skin elasticity and prevent the degradation of collagen. Its use in the cosmetic industry is supported by studies indicating its ability to promote skin health and longevity.

Finally, D-Pyroglutamic acid ethyl ester is explored for its role in neuroscience research. Its ability to modulate certain neurotransmitter pathways makes it a useful compound for studying brain function and exploring new therapeutic avenues for neurodegenerative conditions. As a research tool, it helps in understanding the biochemical mechanisms underlying cognitive processes, which could lead to the development of new treatments for diseases like Alzheimer's and Parkinson's.

1.Inhibition of trigemino-hypoglossal reflex in rats by oxytocin is mediated by mu and kappa opioid receptors.

Zubrzycka M1, Fichna J, Janecka A. Brain Res. 2005 Feb 21;1035(1):67-72.

Recent studies showed that oxytocin plays an important role in the modulation of pain at different levels of the central nervous system. The present study was undertaken to investigate the effect of oxytocin on trigemino-hypoglossal reflex in rats. With the experimental settings used in this study, we have demonstrated that oxytocin showed significant analgesic effect after intracerebroventricular administration in rats, as assayed by the amplitude of the retractory movements of the tongue after tooth pulp stimulation. Antinociceptive effect of oxytocin was inhibited by subsequent perfusion of cerebral ventricles with oxytocin antagonist, [deamino-Cys1-D-Tyr(OEt)2-Thr4-Orn8]-oxytocin, atosiban. An involvement of opioid system in the oxytocin-induced analgesia was studied after intracerebroventricular administration of different opioid antagonists: non-selective naloxone, mu-selective beta-funaltrexamine, delta-selective naltrindole, and kappa-selective nor-binaltorphimine.

2.Opposite effects of oxytocin on proliferation of osteosarcoma cell lines.

Petersson M1. Regul Pept. 2008 Oct 9;150(1-3):50-4. doi: 10.1016/j.regpep.2008.02.007. Epub 2008 Mar 4.

Oxytocin stimulates proliferation of human osteoblast-like (hOB) cells and human osteosarcoma cells (SaOS-2). In contrast, oxytocin has also been shown to inhibit proliferation of other cell lines such as breast cancer cells. The aim of the present study was to investigate the effects of different concentrations of oxytocin on cell proliferation in osteosarcoma cell lines of different stages of differentiation: SaOS-2, TE-85, and UMR-106. For this purpose cells were incubated with oxytocin (1-1000 pmol/l). Cell proliferation was measured by [(3)H]thymidine incorporation and a commercially available kit (EZ4U). Incubation with oxytocin during 24 h increased proliferation of SaOS-2 cells significantly (100 pmol/l: p<0.01). In contrast, 24 h of incubation with oxytocin decreased proliferation of TE-85 (100 pmol/l: p<0.01) and UMR-106 cells significantly (100 pmol/l: p<0.01). The effects of oxytocin in SaOS-2 and TE-85, but not in UMR-106 cells, were abolished when the cells were incubated with both oxytocin and an oxytocin antagonist (1-deamino-2-D-Tyr-(Oet)-4-Thr-8-Orn-oxytocin).

3.Antinociceptive role of oxytocin in the nucleus raphe magnus of rats, an involvement of mu-opioid receptor.

Wang JW1, Lundeberg T, Yu LC. Regul Pept. 2003 Oct 15;115(3):153-9.

Recent studies showed that oxytocin plays an important role in nociceptive modulation in the central nervous system. The present study was undertaken to investigate the role of oxytocin in antinociception in the nucleus raphe magnus (NRM) of rats and the possible interaction between oxytocin and the opioid systems. Intra-NRM injection of oxytocin induced dose-dependent increases in hindpaw withdrawal latencies (HWLs) to noxious thermal and mechanical stimulation in rats. The antinociceptive effect of oxytocin was significantly attenuated by subsequent intra-NRM injection of the oxytocin antagonist 1-deamino-2-D-Tyr-(Oet)-4-Thr-8-Orn-oxytocin. Intra-NRM injection of naloxone dose-dependently antagonized the increased HWLs induced by preceding intra-NRM injection of oxytocin, indicating an involvement of opioid receptors in oxytocin-induced antinociception in the NRM of rats. Furthermore, the antinociceptive effect of oxytocin was dose-dependently attenuated by subsequent intra-NRM injection of the mu-opioid antagonist beta-funaltrexamine (beta-FNA), but not by the kappa-opioid antagonist nor-binaltorphimine (nor-BNI) or the delta-opioid antagonist naltrindole.

4.Involvement of oxytocin and its receptor in nociceptive modulation in the central nucleus of amygdala of rats.

Han Y1, Yu LC. Neurosci Lett. 2009 Apr 17;454(1):101-4. doi: 10.1016/j.neulet.2009.02.062. Epub 2009 Mar 3.

Studies have demonstrated that oxytocin plays important roles in pain modulation in the central nervous system. Oxytocin-ergic neurons are found in paraventricular nucleus and supraoptic nucleus of the hypothalamus. The oxytocin-ergic neurons send fibers from hypothalamus to amygdala and high density of oxytocin receptors are found in the central nucleus of amygdala (CeA). The present study was performed to investigate the influences of oxytocin and its receptors on nociceptive responses in the CeA of rats. Intra-CeA injection of 0.1, 0.5 or 1nmol of oxytocin induced dose-dependent increases in the handpaw withdrawal latency induced by noxious thermal and mechanical stimulation in rats. The oxytocin-induced anti-nociception could be blocked by the selective oxytocin antagonist 1-deamino-2-d-Tyr-(Oet)-4-Thr-8-Orn-oxytocin. The present study demonstrated that oxytocin and its receptors are involved in nociceptive modulation in the CeA of rats.